GB906805A - Improvements in or relating to cyanine and related dyes - Google Patents
Improvements in or relating to cyanine and related dyesInfo
- Publication number
- GB906805A GB906805A GB17899/58A GB1789958A GB906805A GB 906805 A GB906805 A GB 906805A GB 17899/58 A GB17899/58 A GB 17899/58A GB 1789958 A GB1789958 A GB 1789958A GB 906805 A GB906805 A GB 906805A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- complete
- pyrroline
- hydroxy
- nucleus
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000975 dye Substances 0.000 title abstract 4
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- UTBXIKGTARXRTH-UHFFFAOYSA-N 1-hydroxy-2,3-dihydropyrrole Chemical class ON1CCC=C1 UTBXIKGTARXRTH-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract 1
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical class O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 abstract 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 abstract 1
- UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical compound O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 abstract 1
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 abstract 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 abstract 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/10—The polymethine chain containing an even number of >CH- groups
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/08—Sensitivity-increasing substances
- G03C1/10—Organic substances
- G03C1/12—Methine and polymethine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The Specification relates to methine dyes having one of the general formulae:- <FORM:0906805/IV (b)/1> wherein R1, R2, R5 and R8 are each hydrogen or an alkyl group, R3 and R4 are alkyl groups, R6 is an alkyl or aralkyl group, R7 is an alkyl, aryl or aralkyl group, R9 is an alkyl, aryl, aralkyl, carboxyalkyl or carbalkoxyalkyl group, x is 1, 2, 3 or 4, L is -N= or -CH=, n is 1 or 2, m is 1, 2 or 3, D and D1 complete 5- or 6-membered nuclei, Y is an anion and P and Q are acyl, carbalkoxy or cyano groups. They are prepared by the usual processes from the quaternary salts of hydroxy pyrroline bases, described in Specification 906,803. The hydroxy groups in the pyrroline nuclei of the dyes may be esterified by heating with an acid anhydride such as acetic anhydride. In the examples, D may complete a benzthiazole, quinoline, quinazoline or benzoxazole nucleus, or it may be a hydroxy pyrroline nucleus to give a symmetrical dye, D1 may complete a rhodanine, thiohydantoin, thiobarbituric acid or 5-pyrazolone nucleus, and P and Q are both CN or CH3CO.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL239859D NL239859A (en) | 1958-06-04 | ||
| GB17899/58A GB906805A (en) | 1958-06-04 | 1958-06-04 | Improvements in or relating to cyanine and related dyes |
| US813655A US2984663A (en) | 1958-06-04 | 1959-05-18 | Methin dyes containing hydroxypyrroline nuclei |
| DEI16519A DE1170570B (en) | 1958-06-04 | 1959-06-03 | Process for the preparation of dyes with the pyrrole core |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB17899/58A GB906805A (en) | 1958-06-04 | 1958-06-04 | Improvements in or relating to cyanine and related dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB906805A true GB906805A (en) | 1962-09-26 |
Family
ID=10103198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17899/58A Expired GB906805A (en) | 1958-06-04 | 1958-06-04 | Improvements in or relating to cyanine and related dyes |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2984663A (en) |
| DE (1) | DE1170570B (en) |
| GB (1) | GB906805A (en) |
| NL (1) | NL239859A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3124584A (en) * | 1964-03-10 | Process for the production of hetero- |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE466374A (en) * | 1939-02-17 | |||
| US2409612A (en) * | 1939-02-17 | 1946-10-22 | Eastman Kodak Co | Pyrrole dyes |
| DE883025C (en) * | 1940-12-02 | 1953-07-13 | Hoechst Ag | Process for the preparation of sensitizing dyes |
| DE902290C (en) * | 1942-02-20 | 1954-03-22 | Hoechst Ag | Process for the preparation of sensitizing dyes |
| FR54378E (en) * | 1943-12-25 | 1950-03-10 | Ig Farbenindustrie Ag | Sensitizing dyes, pyrrolidic derivatives used in the manufacture of certain of these dyes and processes for preparing these various products |
| US2739148A (en) * | 1951-09-19 | 1956-03-20 | Eastman Kodak Co | Cyanine dyes containing a 3,5-diarylpyrrole nucleus and process of preparation |
-
0
- NL NL239859D patent/NL239859A/xx unknown
-
1958
- 1958-06-04 GB GB17899/58A patent/GB906805A/en not_active Expired
-
1959
- 1959-05-18 US US813655A patent/US2984663A/en not_active Expired - Lifetime
- 1959-06-03 DE DEI16519A patent/DE1170570B/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL239859A (en) | |
| DE1170570B (en) | 1964-05-21 |
| US2984663A (en) | 1961-05-16 |
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